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The Chesapeake to Ourselves

We’d been watching the weather all week and couldn’t have been more pleased. Not only was the sun out, it was downright hot as we checked out our Bavaria 32 at the Horizon Yacht Charters base in the Yacht Haven Marina in Eastport, Annapolis.
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We’d been watching the weather all week and couldn’t have been more pleased. Not only was the sun out, it was downright hot as we checked out our Bavaria 32 at the Horizon Yacht Charters base in the Yacht Haven Marina in Eastport, Annapolis. Setting off around noon, we found plenty of boat traffic in the outer harbor beyond the Severn River, nearly all of it sail-powered. Among the boats enjoying the sun and moderate breezes were a couple of Naval Academy 44s practicing their spinnaker gybes and a small fleet of J/22s mixing things up in the distance. 

I’m the kind of sailor—selfish, perhaps—who likes to have a body of water all to himself as much as possible. But this kind of company I can handle: especially since, with the exception of a tug barge and northbound ro-ro car carrier off in the distance, the rest of the Chesapeake Bay was pretty much empty. 

Balancing Act

The fact that we were seeing so few boats was no accident, nor was it without risk. April on the Chesapeake—“shoulder season” for those in the charter trade—can be either absolutely beautiful or absolutely, well, not so much. And while the days my wife, Shelly, my daughter, Bridget, and I had just spent sightseeing in Washington D.C. would definitely be classified among the former, I knew full well the latter could rear its ugly head at any time. Indeed, as we were checking out, Horizon Yacht Charter’s Hunter Adkisson told me the previous week had been bitterly cold, with strong winds roiling the bay for days on end. The National Weather Service was also calling for rain that coming weekend. But for the next few days, at least, it looked like we’d have clear sailing. 

Making our way south-southeast, we set a course for the iconic Thomas Point Lighthouse. As we continued south, the wind went light and clocked around to the west, so we motored the last couple of miles into the South River. With us was Les Bissell, an old friend from our Peace Corps days, who sails his Irwin Citation 34, Gypsy Night, on the Chesapeake. Over the years, Les and I have made a habit of going for a short fall cruise the weekend of the Annapolis boat show, just as the summer season is winding down. We’ve often stopped in at the anchorage in Selby Bay and decided it would make a good first stop for this latest trip as well. 

Not surprisingly, the bay was almost empty, which was a good thing given the trouble we had getting our anchor to bite. Backing down the first time, I was sure we were set, until I dropped the auxiliary in reverse. Next thing I knew, we were slowly but steadily closing with the low grassy bank to the east and had triggered the anchor alarm that Les and I had been playing with on the chartplotter. 

While it’s never much fun hauling up the anchor up for a do-over, it’s a lot less hassle when you’ve got plenty of maneuvering room. I really don’t think the folks in the one other boat tucked in at the mouth of the creek on the other side of the bay minded. 

Wide Open Spaces

Weighing anchor next morning, we ghosted back down the South River, then hardened up to begin a long beat toward Bloody Point Lighthouse on the opposite shore. Once again, we were pretty much it in terms of boat traffic, with merchant vessels and commercial fishing boats at least as numerous as the recreational craft in the area. The air temperature in the middle of the bay was crisp, but the sun shone bright. It was one of those perfect spring days when you wear a fleece jacket not because you have to, but because it leaves you feeling that much more cozy, not to mention one of those days when you need to guard against an early-season sunburn.

Later, hardening up around Tilghman Point, we threaded our way among the nuns and cans leading to the town of St. Michaels, midway up the Miles River. With its swarms of summer tourists, St. Michaels is typically just about the last place in the world a guy like me wants to go. But Les said it was a different place in the spring, so we decided to give it a try. 

Sure enough, the snug little harbor wasn’t just quieter than I’d expected, it was empty. Pulling alongside the St. Michaels Marina fuel dock for a quick pumpout, I asked the manager about the possibility of getting a slip. “Sure, which one ya want?” he asked, motioning to the scores of empty dock spaces, before assigning us a spot normally reserved for 50-footers.

It was warmer ashore, so after doing battle with a sack of crustaceans at the Crab Claw restaurant, we wandered down Talbot Street to get some ice cream. The wealth of galleries and boutiques served as evidence of the town’s popularity during high season, but on this quiet spring evening we had the place all to ourselves. 

Later, after Bridget had gone to sleep, Shelly, Les and I whiled away the time in the cockpit, drinking beer and reminiscing about our time together in the South Pacific. We had an unobstructed view of the Mill River from our dock and were still pretty much the only boat around. As the harbor lights danced on the glassy water, the surrounding quiet seemed to bring to life the St. Michaels of old, back before the tourists arrived and it was primarily a boatbuilding center and fishing town. Magical. 

Smooth Sailing 

The following morning, we wended our way back through the buoys we’d passed the day before, throwing in a few gybes as we did our best to harness the light air, thankful we didn’t have to worry about being tossed around by a bunch of motorboat wakes. Rounding Tilghman Point, the breeze started to build and we had a great beat back toward Bloody Point Lightouse, where we bore away toward the western shore. Along the way, Les gave Bridget a few pointers on steering, and Bridget—who is more accustomed to sailing Sonars on Boston Harbor—announced she liked wheels much more than tillers. 

A few hours later, after a fine sunny reach across the bay, we short-tacked our way into the West River, where we didn’t have to drop the main until we’d arrived in the anchorage. Once again, we had some problems dragging, so we put out a Danforth to back up our Delta. Les said the former was his go-to hook for getting a firm grip in the area’s mud and clay, and it was a good thing I listened to him: the wind not only went north as forecast, but was piping up to 20-plus knots by the time we awoke the next morning. Getting ready to set sail, the Delta came up almost as easily as it had gone down. But the Danforth felt like it had been set in cement. We eventually had to sail it loose to break its grip on the bottom—which was fine by me.

With the wind still out of the north, we had a great reach back down the river before hardening up for the final beat up to Annapolis. In no time, the wind both built and backed until it was blowing right out of the Severn River. But our Bavaria 32 took it all in stride as we short-tacked our way toward the Naval Academy and the blue dome of the Maryland statehouse. 

After dropping Les off at the dock behind the Chart House restaurant so he could return home to D.C., we grabbed one of the many moorings right off “Ego Alley.” In contrast to every other time I’ve been to Annapolis, there were dozens to spare, with only four other boats joining us. On the downside, the water taxi wasn’t running, which meant we were pretty much trapped because we didn’t have a dinghy of our own. But we still had a fine old time enjoying the remains of the day and munching down the last of our provisions—which included a bottle of white wine, a bag of chips and a half-dozen brats—as we watched the schooner Pride of Baltimore set sail with a boatload of charter guests. 

Next morning we awoke to a low overcast, pumped out at the Yacht Basin Co. and then promptly returned the boat to the friendly folks at Horizon Yacht Charters. Thirty minutes later, as we were strolling up Main Street toward Chick & Ruth’s for some crab cakes, it started to rain. Our timing couldn’t have been better. 

Afterward, we took a lap around Church Circle and strolled among the many historic homes surrounding the statehouse. To someone who has spent the vast majority of his time in Annapolis walking crowded boat show docks, it was a revelation. 

The soft misting rain cast a hush over the entire town as we made our way over brick sidewalks and under trees heavy with new damp leaves. Our favorite spot proved to be a gem called The Annapolis Bookstore on Maryland Avenue: cozy little place that specializes in “used, new, rare & remarkable books” and is awash in a kind of overstuffed Old World charm. For this old sailor, more accustomed to waterside bars and gift shops, it was just the thing for shaking off the chill of a damp afternoon—a glimpse of an Annapolis that I hadn’t even known existed and the perfect ending to our early-springtime adventure on the Chesapeake. 

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